AR130165A1 - HETEROCYCLIC COMPOUNDS, COMPOSITIONS THEREOF AND METHODS OF TREATMENT THEREOF - Google Patents
HETEROCYCLIC COMPOUNDS, COMPOSITIONS THEREOF AND METHODS OF TREATMENT THEREOFInfo
- Publication number
- AR130165A1 AR130165A1 ARP230102106A ARP230102106A AR130165A1 AR 130165 A1 AR130165 A1 AR 130165A1 AR P230102106 A ARP230102106 A AR P230102106A AR P230102106 A ARP230102106 A AR P230102106A AR 130165 A1 AR130165 A1 AR 130165A1
- Authority
- AR
- Argentina
- Prior art keywords
- substituted
- unsubstituted
- cycloalkyl
- heterocyclyl
- alkoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 title abstract 2
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 11
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 4
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 102100030708 GTPase KRas Human genes 0.000 abstract 3
- 101000584612 Homo sapiens GTPase KRas Proteins 0.000 abstract 3
- 102000008300 Mutant Proteins Human genes 0.000 abstract 3
- 108010021466 Mutant Proteins Proteins 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229940002612 prodrug Drugs 0.000 abstract 2
- 239000000651 prodrug Substances 0.000 abstract 2
- 102200006531 rs121913529 Human genes 0.000 abstract 2
- 102200006539 rs121913529 Human genes 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 150000003568 thioethers Chemical class 0.000 abstract 2
- 150000003573 thiols Chemical class 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 230000003321 amplification Effects 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 238000003199 nucleic acid amplification method Methods 0.000 abstract 1
- 230000004952 protein activity Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Se proporcionan en el presente documento compuestos que tienen la siguiente estructura: de fórmula (1), en donde los sustituyentes son como se define en el presente documento, composiciones que comprenden una cantidad efectiva de un compuesto, y métodos para modular la actividad de KRAS G12D y/o G12V. Reivindicación 1: Un compuesto, que tiene la fórmula (1) o una sal, tautómero, isotopólogo, estereoisómero, enantiómero, atropisómero, o profármaco farmacéuticamente aceptable del mismo, en donde el anillo A es arilo sustituido o no sustituido, o heteroarilo sustituido o no sustituido; el anillo B es cicloalquilo sustituido o no sustituido o heterociclilo sustituido o no sustituido; X es N o C-R⁸; cada uno de R⁰ es, de manera independiente, H, halógeno, amino, -CN, -OH, alquilo de C₁₋₄ sustituido o no sustituido, alquenilo de C₁₋₄ sustituido o no sustituido, alquinilo de C₁₋₄ sustituido o no sustituido, alcoxi de C₁₋₄ sustituido o no sustituido, cicloalquilo de C₃₋₅ sustituido o no sustituido, heterociclilo de 3 miembros hasta 5 miembros sustituido o no sustituido, alquilamino de C₁₋₄ sustituido o no sustituido, carboxi, nitro, tiol, o tioéter; o uno o más pares de los grupos R⁰, junto con el átomo al cual estos se enlazan, forman cicloalquilo sustituido o no sustituido, heterociclilo sustituido o no sustituido, arilo sustituido o no sustituido, o heteroarilo sustituido o no sustituido; cada uno de R³ᵃ, R³ᵇ, R⁴ᵃ, R⁴ᵇ, R⁵ᵃ, y R⁵ᵇ, es, de manera independiente, H, halógeno, amino sustituido o no sustituido, -CN, -OH, alquilo de C₁₋₄ sustituido o no sustituido, alcoxi de C₁₋₄ sustituido o no sustituido, cicloalquilo de C₃₋₅ sustituido o no sustituido, heterociclilo de 3 miembros hasta 5 miembros sustituido o no sustituido, alquilamino de C₁₋₄ sustituido o no sustituido, carboxi, nitro, tiol, o tioéter; o de manera opcional, R³ᵃ, y R³ᵇ, junto con el átomo al cual estos se enlazan, forman cicloalquilo sustituido o no sustituido, o heterociclilo sustituido o no sustituido; o R⁴ᵃ, y R⁴ᵇ, junto con el átomo al cual estos se enlazan, forman cicloalquilo sustituido o no sustituido, o heterociclilo sustituido o no sustituido; o R⁵ᵃ, y R⁵ᵇ, junto con el átomo al cual estos se enlazan, forman cicloalquilo sustituido o no sustituido, o heterociclilo sustituido o no sustituido; o los grupos R³ᵃ, y R⁴ᵃ, junto con los átomos a los cuales estos se enlazan, forman cicloalquilo sustituido o no sustituido, o heterociclilo sustituido o no sustituido; o los grupos R³ᵃ, y R⁵ᵃ, junto con los átomos a los cuales estos se enlazan, forman cicloalquilo sustituido o no sustituido, o heterociclilo sustituido o no sustituido; o los grupos R⁴ᵃ, y R⁵ᵃ, junto con los átomos a los cuales estos se enlazan, forman cicloalquilo sustituido o no sustituido, o heterociclilo sustituido o no sustituido; o R⁶ es H, alquilo de C₁₋₈ sustituido o no sustituido, alcoxi de C₁₋₈ sustituido o no sustituido, cicloalquilo de C₁₋₈ sustituido o no sustituido, o heterociclilo de 3 miembros hasta 8 miembros sustituido o no sustituido; R⁸ es H, halógeno, alquilo de C₁₋₄ sustituido o no sustituido, alquenilo de C₁₋₄ sustituido o no sustituido, cicloalquilo de C₃₋₅ sustituido o no sustituido, alcoxilo de C₁₋₄ sustituido o no sustituido, alquilo halogenado de C₁₋₄ sustituido o no sustituido, cicloalquilo halogenado de C₃₋₅ sustituido o no sustituido, alcoxilo halogenado de C₁₋₄ sustituido o no sustituido, CN, OH, o amino; t es 0 o 1; y cada uno de m, y q es, de manera independiente, un entero entre 0 y el número máximo de los grupos sustituyentes permitidos en los anillos A, y B, respectivamente. Reivindicación 70: Un método para inhibir la actividad de la proteína mutante KRAS o amplificación de KRAS en una célula, que comprende poner en contacto dicha célula con una cantidad efectiva de un compuesto de conformidad con cualquiera de las reivindicaciones 1 - 68, o una sal, tautómero, isotopólogo, estereoisómero, enantiómero, atropisómero o profármaco del mismo farmacéuticamente aceptable, de manera opcional en donde la proteína mutante KRAS es la proteína mutante KRAS G12D y/o G12V.Provided herein are compounds having the following structure: of formula (1), wherein the substituents are as defined herein, compositions comprising an effective amount of a compound, and methods of modulating the activity of KRAS G12D and/or G12V. Claim 1: A compound, having the formula (1) or a pharmaceutically acceptable salt, tautomer, isotopologue, stereoisomer, enantiomer, atropisomer, or prodrug thereof, wherein ring A is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; ring B is substituted or unsubstituted cycloalkyl or substituted or unsubstituted heterocyclyl; X is N or C—R⁸; each R⁰ is, independently, H, halogen, amino, -CN, -OH, substituted or unsubstituted C₁₋₄ alkyl, substituted or unsubstituted C₁₋₄ alkenyl, substituted or unsubstituted C₁₋₄ alkynyl, substituted or unsubstituted C₁₋₄ alkoxy, substituted or unsubstituted C₃₋₅ cycloalkyl, substituted or unsubstituted 3- to 5-membered heterocyclyl, substituted or unsubstituted C₁₋₄ alkylamino, carboxy, nitro, thiol, or thioether; or one or more pairs of the R⁰ groups, together with the atom to which they are attached, form substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; each of R³ᵃ, R³ᵇ, R⁴ᵃ, R⁴ᵇ, R⁵ᵃ, and R⁵ᵇ, is independently H, halogen, substituted or unsubstituted amino, -CN, -OH, substituted or unsubstituted C₁₋₄ alkyl, substituted or unsubstituted C₁₋₄ alkoxy, substituted or unsubstituted C₃₋₅ cycloalkyl, substituted or unsubstituted 3- to 5-membered heterocyclyl, substituted or unsubstituted C₁₋₄ alkylamino, carboxy, nitro, thiol, or thioether; or optionally, R³ᵃ and R³ᵇ, together with the atom to which they are attached, form substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl; or R⁴ᵃ, and R⁴ᵇ, together with the atom to which they are bonded, form substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl; or R⁵ᵃ, and R⁵ᵇ, together with the atom to which they are bonded, form substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl; or the groups R³ᵃ, and R⁴ᵃ, together with the atoms to which they are bonded, form substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl; or the groups R³ᵃ, and R⁵ᵃ, together with the atoms to which they are bonded, form substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl; or the groups R⁴ᵃ and R⁵ᵃ, together with the atoms to which they are attached, form substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl; or R⁶ is H, substituted or unsubstituted C₁₋₈ alkyl, substituted or unsubstituted C₁₋₈ alkoxy, substituted or unsubstituted C₁₋₈ cycloalkyl, or substituted or unsubstituted 3- to 8-membered heterocyclyl; R⁸ is H, halogen, substituted or unsubstituted C₁₋₄ alkyl, substituted or unsubstituted C₁₋₄ alkenyl, substituted or unsubstituted C₃₋₅ cycloalkyl, substituted or unsubstituted C₁₋₄ alkoxy, substituted or unsubstituted halogenated C₁₋₄ alkyl, substituted or unsubstituted halogenated C₃₋₅ cycloalkyl, substituted or unsubstituted halogenated C₁₋₄ alkoxy, CN, OH, or amino; t is 0 or 1; and each of m, and q is, independently, an integer between 0 and the maximum number of substituent groups allowed on rings A, and B, respectively. Claim 70: A method of inhibiting KRAS mutant protein activity or KRAS amplification in a cell, comprising contacting said cell with an effective amount of a compound according to any of claims 1 - 68, or a pharmaceutically acceptable salt, tautomer, isotopologue, stereoisomer, enantiomer, atropisomer or prodrug thereof, optionally wherein the KRAS mutant protein is KRAS G12D and/or G12V mutant protein.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2022111871 | 2022-08-11 | ||
| CN2022121125 | 2022-09-23 | ||
| CN2023079087 | 2023-03-01 | ||
| CN2023093212 | 2023-05-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR130165A1 true AR130165A1 (en) | 2024-11-13 |
Family
ID=89850951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP230102106A AR130165A1 (en) | 2022-08-11 | 2023-08-10 | HETEROCYCLIC COMPOUNDS, COMPOSITIONS THEREOF AND METHODS OF TREATMENT THEREOF |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20240262848A1 (en) |
| CN (1) | CN119677754A (en) |
| AR (1) | AR130165A1 (en) |
| AU (1) | AU2023320914A1 (en) |
| TW (1) | TW202417454A (en) |
| WO (1) | WO2024032702A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4489738A1 (en) | 2022-03-11 | 2025-01-15 | Kumquat Biosciences Inc. | Heterocyclic compounds and uses thereof |
| WO2024031088A1 (en) | 2022-08-05 | 2024-02-08 | Kumquat Biosciences Inc. | Heterocyclic compounds and uses thereof |
| WO2024206858A1 (en) | 2023-03-30 | 2024-10-03 | Revolution Medicines, Inc. | Compositions for inducing ras gtp hydrolysis and uses thereof |
| WO2024229406A1 (en) | 2023-05-04 | 2024-11-07 | Revolution Medicines, Inc. | Combination therapy for a ras related disease or disorder |
| WO2024235286A1 (en) * | 2023-05-16 | 2024-11-21 | Hutchmed Limited | Tricyclic compounds and uses thereof |
| WO2025034702A1 (en) | 2023-08-07 | 2025-02-13 | Revolution Medicines, Inc. | Rmc-6291 for use in the treatment of ras protein-related disease or disorder |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018206539A1 (en) * | 2017-05-11 | 2018-11-15 | Astrazeneca Ab | Heteroaryl compounds that inhibit g12c mutant ras proteins |
| CN112574224A (en) * | 2019-09-30 | 2021-03-30 | 上海迪诺医药科技有限公司 | KRAS G12C inhibitor and application thereof |
| AU2022254674A1 (en) * | 2021-04-08 | 2023-10-12 | Genentech, Inc. | Oxazepine compounds and uses thereof in the treatment of cancer |
| EP4489738A1 (en) * | 2022-03-11 | 2025-01-15 | Kumquat Biosciences Inc. | Heterocyclic compounds and uses thereof |
-
2023
- 2023-08-10 AR ARP230102106A patent/AR130165A1/en unknown
- 2023-08-10 TW TW112130032A patent/TW202417454A/en unknown
- 2023-08-10 WO PCT/CN2023/112168 patent/WO2024032702A1/en active Application Filing
- 2023-08-10 AU AU2023320914A patent/AU2023320914A1/en active Pending
- 2023-08-10 CN CN202380058002.3A patent/CN119677754A/en active Pending
-
2024
- 2024-03-06 US US18/597,844 patent/US20240262848A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20240262848A1 (en) | 2024-08-08 |
| AU2023320914A1 (en) | 2025-02-27 |
| TW202417454A (en) | 2024-05-01 |
| CN119677754A (en) | 2025-03-21 |
| WO2024032702A1 (en) | 2024-02-15 |
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